Sodium Carbonate → HCID 86628186, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-[3-{6-[3-bromo-5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-phenoxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (189 mg, 0.27 mmol) in dimethoxyethane (5 mL) was stirred for 5 minutes at room temperature under nitrogen atmosphere. Then, tetrakis(triphenylphosphine)palladium(0) (78 mg, 0.07 mmol) was added at room temperature and the resulting light yellow solution was heated to 80° C. and stirred for 5 minutes. At this period, a solution of phenylboronic acid (99 mg, 0.82 mmol) in ethanol (5 mL) was added followed by a solution of sodium carbonate (86 mg, 0.82 mmol) in water (0.5 mL). The resulting light yellow suspension was stirred for 24 h at reflux. Then, the reaction mixture was cooled to room temperature and diluted with water (20 mL) and ethyl acetate (30 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined organic extracts were washed with water (100 mL) and brine solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtration of the drying agent and removal of the solvent in vacuo gave the colored residue which was purified by using an ISCO 80 column, eluting with 0-30% ethyl acetate in hexanes to afford 4-[3-{6-[5-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-biphenyl-3-yloxy]-hexyl}-(2-(2-ethoxycarbonyl-ethyl)-phenoxy)-butyric acid ethyl ester (85 mg, 45%) as a light brown oil: ES(+)-HRMS m/e calculated for C43H50O8 (M+Na)+ 717.3398, found 717.3405.

Provenance & Evidence